A solid-supported organocatalyst for asymmetric Mannich reaction to construct C2-quaternary indolin-3-ones. Issue 12 (2nd March 2022)

• Record Type: Journal Article
• Authors: An, Jian-Xiong; Yang, Fen-Fen; Wang, Pan; Gu, Zhi-Cheng; Li, Yan; Chen, Lei; Zhao, Yong-Long; He, Bin
• Is Part Of: RSC advances. Volume 12:Issue 12(2022)
• Page Start: 7040
• Page End: 7045
• Publication Date: 2022-03-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra00456a
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A simple and novel solid-supported organocatalyst from a 2-chlorotrityl chloride resin-immobilized 4-hydroxyproline was developed, which has been used for the asymmetric Mannich reaction of 2-aryl-3 H -indol-3-ones and aldehydes/ketones. Abstract : A simple and novel solid-supported organocatalyst from a 2-chlorotrityl chloride resin-immobilized 4-hydroxyproline was developed, and this organocatalyst has been used for the asymmetric Mannich reaction of 2-aryl-3 H -indol-3-ones and aldehydes/ketones. A series of C2-quaternary indolin-3-ones were prepared in good yields (up to 83%) and with excellent diastereoselectivities (up to 20 : 1) and enantioselectivities (up to 99% ee). In addition, the organocatalyst can be recovered by simple filtration and also be reused for the asymmetric Mannich reaction without significant loss of catalytic efficiency.